Composition comprising a mixture of alkoxylated mono-, di- and triglycerides and glycerine

ABSTRACT

The present invention relates to a composition comprising a mixture of alkoxylated mono-, di-, and triglycerides and glycerine of the following formula                    
     R′ representing H or CH 3 , and each of m, n, and l independently representing a number from 0 to 4, the sum of m, n and l being in the range of from 1 to 4, each of B1, B2, and B3 representing H or                    
     wherein R represents an alkyl or alkenyl group having 6 to 22 carbon atoms.; and the weight ratio of triglyceride/diglyceride/monoglyceride monoglyceride/diglyceride/triglyceride being 46 to 90/9 to 35/1 to 15. 
     The invention also relates to methods for the preparation of this composition, to detergent compositions comprising this composition, and to the use of the composition as surfactant or co-surfactant in detergent compositions.

DESCRIPTION

The present invention relates to a composition comprising a mixture ofalkoxylated mono-, di-, and triglycerides and glycerine, to methods forthe preparation of this composition, to detergent compositionscomprising this composition, and to the use of the composition assurfactant or co-surfactant in detergent compositions.

Most of the known detergent compositions use anionic, amphoteric and/ornon-ionic surfactants to obtain a final product showing satisfactoryproperties in terms of detergency and foam profile. However, most ofthese compositions are generally not satisfactory regarding the problemof ecotoxicity and the irritation to the eyes and the skin.

EP 0 586 323 B1 discloses detergent compositions showing improvedproperties regarding the ecotoxicity and the irritation to the eyes andto the skin. These compositions comprise the mono-, di- and tri-estercompounds represented by the following formula, wherein the weight ratioof mono-, di-, and tri-ester is 46-90/9-30/1-15:

wherein R′ represents H or CH₃, B represents H or

wherein R represents an alkyl or alkenyl group having 6 to 22 carbonatoms, and each of m, n, and l may have a value between 0 to 40, the sumof m, n and l being in the range of from 2 to 100.

The viscosity of compositions disclosed in EP 0 586 323 B1 having a goodfoaming power is generally low. Although the viscosity may be increasedwhen the alkoxylation degree is lowered, this is generally notpreferred, since then the foaming power is also dramatically decreased.Therefore, a salt such as sodium chloride is generally added in order toincrease the viscosity. However, adding a salt leads to an enhancedirritation of the skin and the eyes.

In view of this prior art it was the problem underlying the presentinvention to provide compositions showing a high viscosity and good foamstability, while also showing the good properties with respect tobiodegradability and irritation to the eyes and the skin.

This problem is surprisingly solved by a composition comprising

(i) compounds represented by the following formula (I), wherein each ofB1, B2 and B3 independently represent a group represented by thefollowing formula (II);

(ii) compounds represented by the following formula (I), wherein two ofB1, B2 and B3 independently represent a group represented by thefollowing formula (II), the remainder representing H;

(iii) compounds represented by the following formula (I), wherein one ofB1, B2 and B3 represents a group represented by the following formula(II); the remainder representing H;

(iv) compounds represented by the following formula (I), wherein each ofB1, B2 and B3 represent H;

the weight ratio of the compounds (i)/(ii)/(iii) (iii)/(ii)/(i) being 46to 90/9 to 35/1 to 15:

Formula (I)

R′ representing H or CH₃, and each of m, n, and l independentlyrepresenting a number from 0 to 4, the sum of m, n and l being in therange of 1 to 4;

Formula (II):

wherein R represents an alkyl or alkenyl group having 6 to 22 carbonatoms.

The weight ratio of the compounds (i)/(ii)/(iii) (iii)/(ii)/(i) in thecomposition of the present invention is preferably 60 to 83/16 to 35/1to 6.

Particularly preferred are compounds of formula (I) wherein R′ informula (I) represents H, that is, the compounds are ethoxylatedderivatives.

The sum of m, n and l in formula (I) is in the range of 1 to 4,preferably 1.5 to 3.0, more preferably in the range of 1.5 to smallerthan 2.

The weight ratio (i)+(ii)+(iii)/(iv) is preferably in the range of 85/15to 40/60, more preferably in the range 80/20 to 45/55.

The compositions of the present invention can be prepared by a firstmethod comprising the following steps:

a) Subjecting a mixture of glycerine and a compound of the followingformula (III) to an interesterification reaction:

wherein R represents an alkyl or alkenyl group having 6 to 22 carbonatoms, and

b) subjecting the reaction mixture obtained in step a) to analkoxylation using an alkylene oxide having 2 or 3 carbon atoms in thepresence of an alkaline catalyst.

The interesterification reaction in step a) is governed by statistics.Consequently, the molar ratio of the compounds (i), (ii), (iii), and(iv) in the final product is determined by the ratio of the startingmaterials glycerine and the compound of formula (III). The subsequentalkoxylation reaction of step b) is a reaction which generally proceedsquantitatively, so that the amount of alkylene oxide used determines thealkoxylation degree (that is, the sum of m, n, and l). The molar ratioof the compounds (i), (ii), (iii), and (iv) is not affected by thealkoxylation, since the alkylene oxide only reacts with the remainingfree hydroxyl groups in the mono- and di-ester molecules and theglycerine. However, the weight ratio of the compounds (i), (ii), (iii),and (iv) is consequently changed. Since the outcome of both reactionsteps a) and b) can be predicted by the skilled person, modellingcalculations can be employed to determine the correct ratio of thestarting materials for a specific predetermined weight ratio of thecompounds (i), (ii), (iii), and (iv) and a specific predeterminedalkoxylation degree.

The compound of formula (III) includes natural fat and oil as well assynthetic triglycerides. Preferred is a fat or oil including vegetableoil such as coconut oil; palm oil; palm kernel oil; sunflower oil; rapeseed oil; castor oil; olive oil; soybean oil; and animal fat such astallow, bone oil; fish oil; hardened oils and semihardened oils thereof,and mixtures thereof. Particularly preferred are coconut oil, palm oiland tallow such as beef tallow.

Further, the composition of the present invention can be produced by asecond method comprising the following steps:

a′) Reacting a mixture of glycerine and alkylene oxide having 2 or 3carbon atoms in the presence of an alkaline catalyst.

b′) Reacting the reaction mixture obtained in step a′) with a compoundof the following formula (IV).

 wherein R is defined as above for formula (III) and X represents amethyl group or H.

The degree of alkoxylation in the final product (that is, the sum of m,n, and l) is determined by the amount of alkylene oxide employed in stepa′). Step b′) then determines the molar ratio and the weight ratio ofthe compounds (i), (ii), (iii), and (iv). Again, the outcome of bothreaction steps a′) and b′) can be predicted by the skilled person, sothat modelling calculations can be employed to determine the correctratio of the starting materials for a specific predetermined weightratio of the compounds (i), (ii), (iii), and (iv) and a specificpredetermined alkoxylation degree.

The compound of formula (IV) is preferably derived from one of the fatsor oils which are preferably used in the first method of the presentinvention and which are listed above. Particularly preferred are tallowfatty acid and coconut oil fatty acid, palm oil fatty acid, or a methylester thereof.

The composition of the present invention is preferably used as asurfactant or co-surfactant in detergent compositions in which they arepreferably contained in an amount of from 0.5 to 20 wt. %, morepreferably 1 to 8 wt. %.

The detergent compositions of the present invention may additionallycontain one or more of the following additives, depending on the purposeof the detergent composition, this list being non-limiting.

1. Anionic surfactants such as sodium alkyl ether sulphate, ammoniumalkyl ether sulphate, triethanolamine alkyl ether sulphate, sodium alkylsulphate, ammonium alkyl sulphate, triethanolamine alkyl sulphate,sodium alpha-olefin sulphonate, sodium alkyl sulphonate,sulphosuccinates, and sulphosuccinamates.

2. Fatty acids or soaps derived from natural or synthetic sources suchas coco, oleic, soya and tallow fatty acids.

3. Ethoxylated alcohols.

4. Esters of fatty acids from natural or synthetic sources such asglycol, ethylene glycol, diethylene glycol, propylene glycol,dipropylene glycol, saccharose, glucose or polyglycerine.

5. Ethoxylated fatty esters from fatty acids of hydroxy-fatty acids.

6. Amphoteric surfactants such as alkyl amidopropyl betaine, alkylbetaine, alkyl amidopropyl sulphobetaine, alkyl sulphobetaine,cocoamphoacetates, and cocoamphodiacetates.

7. Amine oxides such as dimethyl alkylamine oxides or alkylamidopropylamine oxides.

8. Amides such as monoethanolamides, diethanolamides, ethoxylated amidesor alkylisopropanolamides.

9. Alkylpolyglycosides.

10. Ether carboxylates from alcohols, ethoxylated fatty alcohols.

11. Cationic surfactants such as dialkyl dimethyl ammonium halides,alkyl benzyl dimethyl ammonium halides, alkyl trimethyl ammoniumhalides, esterquats derived from triethanolamine, methyldiethanolamine,dimethylaminopropanediol and oligomers of such esterquats.

12. Additives to improve such formulations, such as thickeners, pearlingagents, opacifiers, antioxidants, preservatives, colorants or parfumes.

EXAMPLES

Compositions of the present invention were prepared according to thefollowing methods; the values for the indicated parameters X, X′, s, m,m′, n, n′, Y, Y′, Z, Z′ are shown in tables I and II:

Method 1: From Triglyceride

X g (X′ moles) of triglyceride (coconut oil or palm oil), m (m′ moles)of glycerine and s g of KOH 85% as catalyst are placed in a 2 kg flaskproperly equipped. The system is purged several times with nitrogen,vacuum stripping is carried out until 110° C., and heating is continuedto 140° C. When the temperature reaches 140° C. the reactor ispressurised to 2-3 Kg/cm² with ethylene oxide added until a total of n g(n′ moles).

Method 2: From Methyl Ester

m g (m′ moles) of glycerine and s g KOH 85% as catalyst are placed in a2 Kg flask properly equipped. The system is purged several times withnitrogen, vacuum stripping is carried out until 110° C. and heating iscontinued to 140° C. When the temperature reaches 140° C., the reactoris pressurised to 2-3 Kg/cm² with ethylene oxide added until a total ofn g (n′ moles). After the final charges of ethylene oxide, the reactionmixture is allowed to react for about ½ hour, z g (z′ moles) of a methylester of fatty acid (either coconut oil fatty acid or palmoil fattyacid), is added and mixed for 45 minutes. Finally, the product is cooledand discharged from the reactor.

Method 3: From Fatty Acid

m g (m′ moles) of glycerine and s g KOH 85% as catalyst are placed in a2 Kg flask properly equipped. The system is purged several times withnitrogen, vacuum stripping is carried out until 110° C. and heating iscontinued to 140° C. When the temperature reaches 140° C., the reactoris pressurised to 2-3 Kg/cm² with ethylene oxide added until a total ofn g (n′ moles). After the final charges of ethylene oxide, the reactionmixture is allowed to react for about ½ hour, y g (y′ moles) of a fattyacid (either coconut oil fatty acid or palm oil fatty acid), is addedand mixed for 45 minutes. Finally, the product is cooled and dischargedfrom the reactor.

The weight ratios of the mono-, di-, and triglycerides obtained by theabove methods is also indicated in Tables I and II.

Then, detergent compositions were prepared with the composition of thepresent invention in an amount of 5 wt. % and sodium laurylethersulphatein an amount of 15 wt. %, the balance being water. Sodium chloride wasadded in the amount indicated in Tables I and II (in wt. %).

The viscosity of the compositions was then measured with a Brookfieldviscosimeter at 20° C. For each experiment, a viscosity curve wasprepared in order to determine the maximum (values given in cps).

The foam ability was measured at 5 seconds with a Ross-Miles apparatususing water at a temperature of 20° C. and a hardness of 20° HF. (valuesgiven in millimeters height).

The results are summarized in Tables I and II.

TABLE I Examples according to the present invention Mixtures of 15%Active Matter of Sodium Laurylether Sulphate + 5% product EXAMPLES A A′B D E E′ F F′ G H Comp. Mono 69 69 69 77 70 70 77 77 71 78 Di 28 28 2822 27 27 21 21 26 20 Tri 3 3 3 2 3 3 2 2 3 2 Alkyl chain Coco Palm CocoCoco Coco Palm Coco Palm Coco Coco (R) EO 1.88 1.88 1.76 1.4 2.5 2.5 2.52.5 3.5 3.5 Prep. way Method 1 3 1 3 1 1 3 1 3 3 Tri- 461.8 470.3 422.3476.4 400 glyceride (x) moles trg 0.69 0.7 0.63 0.57 0.48 (x′) FattyAcid 494.3 396 329.8 351 286.2 (y) moles FA 1.85 1.87 1.56 1.66 1.35(y′) Methyl- ester (z) moles ME (z′) Glycerine 252.1 283.8 256.8 382230.6 209 318 248.5 253.9 276 (m) moles gly 2.74 3.09 2.79 4.15 2.512.27 3.46 2.7 2.76 3 (m′) Ethylene 283.4 255.2 270.2 255.7 344.6 312.3380.2 349.6 424.9 462 Oxide (n) moles (n′) 6.44 5.8 6.14 5.81 7.83 7.18.64 7.95 9.66 10.5 KOH (85%) 2.7 1.2 2.7 1.2 2.4 2.2 1 1.8 1 0.8 (s)Max visc. 45000 80000 43000 15000 22000 35000 18000 25000 26000 36000Salt nec. 2.5 2.5 2.5 6 3.5 3.5 4 4 3.5 4 Foam 175 170 175 175 170 170175 170 170 180

TABLE II Comparative Examples Mixtures of 15% Active Matter of SodiumLaurylether Sulphate + 5% product EXAMPLES C I J K L M N O Comp. Mono 9040 59 77 46 79 69 57 Di 10 46 35 21 42 19 28 36 Tri 0 17 6 2 12 1 3 7Alkyl chain (R) Coco Coco Coco Coco Coco Coco Coco Tallow EO 2.2 2.2 4.40.8 3.5 4.4 15 9.9 Prep. way Method 1 1 1 1 1 1 1 2 Tri-glycerid (x)197.2 670.3 422.8 470 561.2 266.1 187.5 moles trg (x′) 0.29 0.99 0.630.7 0.83 0.39 0.28 Fatty Acid (y) moles FA (y′) Methyl-ester (z) 369moles ME (z′) 1.3 Glycerine (m) 376.8 111.8 146 363.6 114.9 211.3 76.8119.3 moles gly (m′) 4.1 1.22 1.59 3.95 1.25 2.3 0.83 1.3 Ethylene Oxide424.8 213.9 428.7 163.7 320.6 521.1 734.6 564.7 (n) moles (n′) 9.65 4.869.74 3.72 7.29 11.84 16.7 12.83 KOH (85%) (s) 1.2 3.7 2.6 2.4 3.1 1.51.1 1.6 Max visc. 4000 6000 13000 8000 7000 9000 5000 4000 Salt nec. 5 63 4 5 4 4 4 Foam 170 175 175 130 160 155 145 120

As may be derived from the results above, when the ethoxylation degreeis larger than 4 (Ex. J, M, N, O), maximum viscosity is always lowerthan 14000 cps measured with a Brookfield viscosimeter at 20° C. Whenthe ethoxylation degree is lower than 1 (Ex. K) viscosity is also lowerthan 14000 cps. When the triester content is lower than 1 (Ex. C;90/10/0), maximum viscosity is also very low (lower than 14000 cps).When the diester content is too high (Ex. I: 40/46/17 and Ex L:46/42/12), then the viscosity is also lower than 14000 cps.

However, when the samples are within the alkoxylation degree inaccordance with the present invention (1 to 4 EQ mols), viscosities areconsiderably higher (see Table I). Specially this behaviour is enhancedwhen the EQ mols are between 1.5 and 3 (Ex A, A′, B, E, E′, F, F′).

Formulations containing the composition of the present invention areexemplified by the following:

The detergent compositions of the present invention may be formulated asshampoos, baby shampoos, conditioning shampoos, bath gels, hairconditioners, for manual dishwashing, and as all purpose cleaners whichare exemplified below (all values indicated are weight percentages):

Baby Shampoo BS1 BS2 COMPONENTS Deionized water to 100 to 100 SodiumLauryl sulfate (27% 25.0 8.0 Dry) (Emal ® 227E from Kao) SodiumCocoamphoacetate (40% 7.5 15.0 Dry) (Betadet ® SHC-2 from Kao) Example Aproduct 2.0 2.0 Lauryl hydroxysultaine (45% 4.0 Dry) (Betadet ® S-20from Kao) PEG-20 Sorbitan Laurate — 1.0 (Kaopan ® TW-L-120 from Kao)PEG-120 Methylglucose dioleate — 0.2 (Glucamate-DOE-120 ® from Amerchol)NaCl 0.2 — Preservative 0.05 0.05 ANALYSIS Appearance TransparentTransparent viscous viscous liquid liquid pH (100%) 6.5-7.5 6.5-7.5Viscosity (cps) 20° C. 5000-7000 1000-2000 Turbidity point (° C.) <0 <0% Dry matter 12.5-14.5 10.5-12.5 Stability OK OK Shampoo COMPONENTSDeionized water to 100 Sodium Lauryl sulfate (70% Dry) 23.0 (Emal ® 270Efrom Kao) Cocoamidopropoxybetaine (48% Dry) 10.0 (Betadet ® HR-50K fromKao) Example B product 1.8 Pearling agent (Danox ® P-15 3.0 from Kao)Perfume e.q. NaCl e.q. Preservative e.q. ANALYSIS Appearance Pearledviscous liquid pH (100%) 6.0-7.0 Viscosity (cps) 20° C. ≈8000 % Drymatter 24-26 Stability OK Conditioning shampoo COMPONENTS Deionizedwater to 100 Sodium Lauryl sulfate (27% Dry) 32.0 (Emal ® 227E from Kao)Sodium Cocoamphoacetate (40% Dry) 7.5 (Betadet ® SHC-2 from Kao) ExampleE product 3.5 Lauryl hydroxysultaine (45% Dry) 5.0 (Betadet ® S-20 fromKao) Oleic esterquat (80% Dry Matter) 0.5 (Tetranyl ® CO-40 from Kao)Pearling agent (Danox ® BF-22 3.0 from Kao) Perfume e.q. NaCl e.q.Preservative e.q. ANALYSIS Appearance Pearled viscous liquid pH (100%)6.0-6.5 Viscosity (cps) 20° C. ≈7000 % Dry matter 19-21 Stability OKBath gel COMPONENTS Deionized water to 100 Sodium Lauryl sulfate (27%Dry) 37.0 (Emal ® 277 E from Kao) Cocoamidopropoxybetaine (34% Dry) 10.0(Betadet ® HR from Kao) Example F product 2.5 Perfume 0.5 NaCl 0.5Preservative Kathoe CG ® 0.05 from Rohm & Haas EDTA.Na₂ 0.05 ANALYSISAppearance Transparent viscous liquid pH (100%) 5.0-6.0 Viscosity (cps)20° C. 6000-8000 Turbidity point (° C.) <0 % Dry matter 18-20 StabilityOK Hair conditioner HC1 HC2 COMPONENTS Deionized water to 100 to 100Propyleneglycol 2.0 2.0 Dioleic esteruat (80% Dry 1.9 — Matter)(Tetranyl ® CO-40 from Kao) Cetrimonium Chloride (25% Dry) — 6.0(Quartamin ® 60W25 from Kao) Cetearyl alcohol (Kalcol ® 6870 3.0 3.0from Kao) Example A product 0.5 0.5 Perfume e.q. e.q. Preservative e.q.e.q. ANALYSIS Appearance White White viscous viscous emulsion emulsionpH (100%) 4-6 4-6 Viscosity (cps) 20° C. ≈5000 ≈5000 % Dry matter4.5-5.5 4.5-5.5 Stability OK OK Manual dishwashing MD1 MD3 COMPONENTSDeionized water to 100 to 100 Na Laurylethersulfate (70% 9.5 17.0 Dry)(Emal ® 270E from Kao) Sodium C14-16 Olefin Sulfoeate 27.0 14.7 (37%Dry) (Alfanox ® 46 from Kao) Cocoamidopropoxybetaine (34% 2.0 2.0 Dry)(Betadet ® HR) Cocoamid DEA (Amidet ® B-112 1.0 1.0 from Kao) Example E′product 2.0 2.0 NaCl 2.0 1.5 Formaldehyde 40% 0.1 0.1 ANALYSISAppearance Transparent Transparent viscous viscous liquid liquid pH(100%) 6.5-7.5 6.5-7.5 Viscosity (cps) 20° C. 400-800 400-800 Turbiditypoint (° C.) −6 −4 % Dry matter 22-24 22-24 Washed dishes 17 17Stability OK OK All purpose cleaner COMPONENTS Deionized water to 100Sodium C14-16 Olefin Sulfonate 14.6 (37% Dry) (Alfanox ® 46 from Kao)Example E′ product 2.0 Tetrapotassium pyrophosphate 3.0 Butylglycol 1.0EDTA.Na₄ 2.3 Perfume e.q. Preservative e.q. ANALYSIS AppearanceTransparent liquid pH (100%) 7.0-8.0 Viscosity (cps) 20° C. <10 % Drymatter 13.0-14.0 Stability OK

What is claimed is:
 1. Composition comprising (i) compounds representedby the following formula (I), wherein each of B1, B2 and B3independently represent a group represented by the following formula(II); (ii) compounds represented by the following formula (I), whereintwo of B1, B2 and B3 independently represent a group represented by thefollowing formula (II), the remainder representing H; (iii) compoundsrepresented by the following formula (I), wherein one of B1, B2 and B3represents a group represented by the following formula (II); theremainder representing H; (iv) compounds represented by the followingformula (I), wherein each of B1, B2 and B3 represent H; the weight ratioof the compounds (i)/(ii)/(iii) (iii)/(ii)/(i) being 46 to 90/9 to 35/1to 15: Formula (I):

R′ representing H or CH₃, and each of m, n, and l independentlyrepresenting a number from 0 to 4 1, the sum of m, n and l being in therange of 1 to 4 in formula (I) is from 1 to smaller than 2; Formula(II):

wherein R represents an alkyl or alkenyl group having 6 to 22 carbonatoms.
 2. Composition according to claim 1, wherein the weight ratio ofthe compounds (i)/(ii)/(iii) (iii)/(ii)/(i) is 60 to 83/16 to 35/1 to 6.3. Composition according to claim 1, wherein R′ in formula (I)represents H.
 4. Composition according to claim 1, wherein the sum of m,n and l in formula (I) is in the range of 1.5 to 3.0.
 5. Compositioncomprising (i) compounds represented by the following formula (I),wherein each of B1, B2 and B3 independently represent a grouprepresented by the following formula (II); (ii) compounds represented bythe following formula (I), wherein two of B1, B2 and B3 independentlyrepresent a group represented by the following formula (II), theremainder representing H; (iii) compounds represented by the followingformula (I), wherein one of B1, B2 and B3 represents a group representedby the following formula (II); the remainder representing H; (iv)compounds represented by the following formula (I), wherein each of B1,B2 and B3 represent H; the weight ratio of the compounds (i)/(ii)/(iii)(iii)/(ii)/(i) being 60 to 83/16 to 35/1 to 6: Formula (I):

R′ representing H, and each of m, n, and l independently representing anumber from 0 to 4, the sum of m, n and l being in the range of 1.5 to3.0; Formula (II):

wherein R represents an alkyl or alkenyl group having 6 to 22 carbonatoms.
 6. Composition according to claim 5, wherein the sum of m, n andl in formula (I) is smaller than
 2. 7. Composition according to claim 5,wherein the weight ratio (i)+(ii)+(iii)/(iv) is in the range of 85/15 to40/60.
 8. Method for the preparation of a composition comprising (i)compounds represented by the following formula (I), wherein each of B1,B2 and B3 independently represent a group represented by the followingformula (II); (ii) compounds represented by the following formula (I),wherein two of B1, B2 and B3 independently represent a group representedby the following formula (II), the remainder representing H; (iii)compounds represented by the following formula (I), wherein one of B1,B2 and B3 represents a group represented by the following formula (II);the remainder representing H; (iv) compounds represented by thefollowing formula (I), wherein each of B1, B2 and B3 represent H; theweight ratio of the compounds (i)/(ii)/(iii) (iii)/(ii)/(i) being 46 to90/9 to 35/1 to 15: Formula (I):

R′ representing H or CH₃, and each of m, n, and l independentlyrepresenting a number from 0 to 4, the sum of m, n and l being in therange of 1 to 4; Formula (II):

wherein R represents an alkyl or alkenyl group having 6 to 22 carbonatoms; the method comprising the following steps: a) subjecting amixture of glycerine and a compound of the following formula (III) to aninteresterification reaction:

 wherein R represents an alkyl or alkenyl group having 6 to 22 carbonatoms, and b) subjecting the reaction mixture obtained in step a) to analkoxylation using an alkylene oxide having 2 or 3 carbon atoms in thepresence of an alkaline catalyst.
 9. Method for the preparation of acomposition comprising (i) compounds represented by the followingformula (I), wherein each of B1, B2 and B3 independently represent agroup represented by the following formula (II); (ii) compoundsrepresented by the following formula (I), wherein two of B1, B2 and B3independently represent a group represented by the following formula(II), the remainder representing H; (iii) compounds represented by thefollowing formula (I), wherein one of B1, B2 and B3 represents a grouprepresented by the following formula (II); the remainder representing H;(iv) compounds represented by the following formula (I), wherein each ofB1, B2 and B3 represent H; the weight ratio of the compounds(i)/(ii)/(iii) (iii)/(ii)/(i) being 46 to 90/9 to 35/1 to 15: Formula(I):

R′ representing H or CH₃, and each of m, n, and l independentlyrepresenting a number from 0 to 4, the sum of m, n and l being in therange of 1 to 4; Formula (II):

wherein R represents an alkyl or alkenyl group having 6 to 22 carbonatoms; the method comprising the following steps: a′) reacting a mixtureof glycerine and alkylene oxide having 2 or 3 carbon atoms in thepresence of an alkaline catalyst, and b′) reacting the reaction mixtureobtained in step a′) with a compound of the following formula (IV):

 wherein R represents an alkyl or alkenyl group having 6 to 22 carbonatoms, and X represents a methyl group or H.
 10. Detergent compositioncontaining a composition comprising the following compounds (i) to (iv)in an amount of 0.5 to 20 wt.-%. (i) compounds represented by thefollowing formula (I), wherein each of B1, B2 and B3 independentlyrepresent a group represented by the following formula (II); (ii)compounds represented by the following formula (I), wherein two of B1,B2 and B3 independently represent a group represented by the followingformula (II), the remainder representing H; (iii) compounds representedby the following formula (I), wherein one of B1, B2 and B3 represents agroup represented by the following formula (II); the remainderrepresenting H; (iv) compounds represented by the following formula (I),wherein each of Bi B1, B2 and B3 represent H; the weight ratio of thecompounds (i)/(ii)/(iii) (iii)/(ii)/(i) being 46 to 90/9 to 35/1 to 15:Formula (I):

R′ representing H or CH₃, and each of m, n, and l independentlyrepresenting a number from 0 to 4, the sum of m, n and l being in therange of 1 to 4; Formula (II):

wherein R represents an alkyl or alkenyl group having 6 to 22 carbonatoms.
 11. Detergent composition containing a composition comprising thefollowing compounds (i) to (iv) in an amount of 1 to 8 wt.-%. (i)compounds represented by the following formula (I), wherein each of B1,B2 and B3 independently represent a group represented by the followingformula (II); (ii) compounds represented by the following formula (II)(I) wherein two of B1, B2 and B3 independently represent a grouprepresented by the following formula (II), the remainder representing H;(iii) compounds represented by the following formula (I), wherein one ofB1, B2 and B3 represents a group represented by the following formula(II); the remainder representing H; (iv) compounds represented by thefollowing formula (I), wherein each of B1, B2 and B3 represent H; theweight ratio of the compounds (i)/(ii)/(iii) (iii)/(ii)/(i) being 60 to83/16 to 35/1 to 6: Formula (I):

R′ representing H, and each of m, n, and l independently representing anumber from 1 to 4, the sum of m, n and l being in the range of 1.5 to3.0; Formula (II):

wherein R represents an alkyl or alkenyl group having 6 to 22 carbonatoms.